[Cl:1][C:2]1[CH:7]=[C:6]([NH:8]C(OCC)=O)[CH:5]=[CH:4][C:3]=1[CH2:14][N:15]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[CH2:17][O:16]1.I[Si](C)(C)C.Cl>C(Cl)(Cl)Cl>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:14][N:15]2[C:19](=[O:20])[C:18]([CH3:21])([CH3:22])[CH2:17][O:16]2)=[C:2]([Cl:1])[CH:7]=1To a stirred suspension of 8.4 grams (0.026 mole) of 2-[2-chloro-4-(ethoxycarbonylamino)phenyl]methyl-4,4-dimethyl-3-isoxazolidinone in 100 ml of chloroform, under an argon atmosphere and at ambient temperature, was carefully added dropwise 6.0 grams (0.03 mole) of iodotrimethylsilane. Upon completion of addition the reaction mixture was warmed to 60° C. where it stirred for 16 hours. Five ml of methanolic 2N hydrochloric acid was added to the reaction mixture. The solution was stirred for 10 minutes, then concentrated under reduced pressure to a residual solid. The solid was triturated in 25 ml of water. The water/solid mixture was neutralized with aqueous saturated sodium bicarbonate solution. The solid was collected by filtration to give 2-(4-amino-2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 106°-108° C.
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